JPS59213717A - ポリウレタンの製造法 - Google Patents
ポリウレタンの製造法Info
- Publication number
- JPS59213717A JPS59213717A JP58244930A JP24493083A JPS59213717A JP S59213717 A JPS59213717 A JP S59213717A JP 58244930 A JP58244930 A JP 58244930A JP 24493083 A JP24493083 A JP 24493083A JP S59213717 A JPS59213717 A JP S59213717A
- Authority
- JP
- Japan
- Prior art keywords
- seconds
- acid
- dimethylimidazole
- undecene
- diazabicyclo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 22
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title claims description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000004814 polyurethane Substances 0.000 claims abstract description 5
- 229920002635 polyurethane Polymers 0.000 claims abstract description 5
- DTKANQSCBACEPK-UHFFFAOYSA-N n',n'-bis[3-(dimethylamino)propyl]-n,n-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCN(CCCN(C)C)CCCN(C)C DTKANQSCBACEPK-UHFFFAOYSA-N 0.000 claims abstract 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 2
- 239000005642 Oleic acid Substances 0.000 claims 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 239000006260 foam Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 9
- 239000006071 cream Substances 0.000 description 5
- 229920005903 polyol mixture Polymers 0.000 description 5
- 238000000465 moulding Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- 102100020740 Dolichol phosphate-mannose biosynthesis regulatory protein Human genes 0.000 description 1
- 101000932183 Homo sapiens Dolichol phosphate-mannose biosynthesis regulatory protein Proteins 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- -1 casting Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/494,198 US4431753A (en) | 1983-05-13 | 1983-05-13 | Catalyst blend containing 1,2-dimethylimidazole |
| US494198 | 1990-03-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59213717A true JPS59213717A (ja) | 1984-12-03 |
| JPS6366848B2 JPS6366848B2 (enrdf_load_stackoverflow) | 1988-12-22 |
Family
ID=23963461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58244930A Granted JPS59213717A (ja) | 1983-05-13 | 1983-12-27 | ポリウレタンの製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4431753A (enrdf_load_stackoverflow) |
| EP (1) | EP0125346B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS59213717A (enrdf_load_stackoverflow) |
| AT (1) | ATE30731T1 (enrdf_load_stackoverflow) |
| DE (1) | DE3374414D1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009242600A (ja) * | 2008-03-31 | 2009-10-22 | Aica Kogyo Co Ltd | ウレアウレタン樹脂組成物 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585803A (en) * | 1984-08-17 | 1986-04-29 | The Dow Chemical Company | Internal mold release compositions |
| US4935453A (en) * | 1988-11-30 | 1990-06-19 | Ashland Oil, Inc. | Thermoset molding compositions catalyzed by keto-enol salt and 1,8-diaza-bicyclo(5.4.0)undec-7-ene |
| JP2832276B2 (ja) * | 1989-06-30 | 1998-12-09 | テイ・エステック株式会社 | ウレタンフォーム成形品の製造方法 |
| JP3044261B2 (ja) * | 1990-04-11 | 2000-05-22 | 東ソー株式会社 | 通気性に優れた軟質ポリウレタンフォ−ムの製造法 |
| US5334620A (en) * | 1992-06-10 | 1994-08-02 | Basf Aktiengesellschaft | Production of chlorofluorocarbon-free, urethane-containing moldings having a cellular core and a compacted peripheral zone |
| DE69509690T2 (de) * | 1994-03-18 | 1999-09-23 | Air Products And Chemicals, Inc. | Amin-Katalysatoren mit niedrigem Geruch für auf Polyester-Polyole basierte Polyurethan-Blockweichschaumstoffe |
| US8258198B2 (en) | 2004-05-28 | 2012-09-04 | Air Products And Chemicals, Inc. | Fast demold/extended cream time polyurethane formulations |
| JP4874689B2 (ja) * | 2006-03-31 | 2012-02-15 | 富士フイルム株式会社 | ホログラフィック記録用組成物及びこれを用いた光記録媒体 |
| EP2465886A1 (de) * | 2010-12-16 | 2012-06-20 | Bayer MaterialScience AG | Polyisocyanat-Polyadditionsprodukte, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3010963A (en) * | 1959-05-21 | 1961-11-28 | Houdry Process Corp | Quaternary hydroxyalkyl tertiary heterocyclic amine bases and salts |
| US3152094A (en) * | 1960-08-26 | 1964-10-06 | Air Prod & Chem | Production of polyurethanes using an imidazole catalyst |
| CH441756A (de) * | 1961-01-17 | 1967-08-15 | Air Prod & Chem | Katalysator für die Polymerisation von Isocyanaten und für Isocyanat-Additionsreaktionen |
| DE1222666B (de) * | 1964-10-20 | 1966-08-11 | Basf Ag | Verfahren zur Herstellung von Polyurethanschaumstoffen |
| US3448065A (en) * | 1965-09-07 | 1969-06-03 | Air Prod & Chem | Polyurethane catalysis employing n-hydroxyalkyl substituted imidazole |
| GB1182014A (en) * | 1966-10-29 | 1970-02-25 | San Abbott Ltd | Urethane and Urea Catalyst |
| US3728291A (en) * | 1971-06-21 | 1973-04-17 | Air Prod & Chem | Catalyst composition for polyurethane foam |
| US4255528A (en) * | 1979-09-24 | 1981-03-10 | Abbott Laboratories | Polyurethane process |
-
1983
- 1983-05-13 US US06/494,198 patent/US4431753A/en not_active Expired - Fee Related
- 1983-12-24 EP EP83113102A patent/EP0125346B1/en not_active Expired
- 1983-12-24 AT AT83113102T patent/ATE30731T1/de not_active IP Right Cessation
- 1983-12-24 DE DE8383113102T patent/DE3374414D1/de not_active Expired
- 1983-12-27 JP JP58244930A patent/JPS59213717A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009242600A (ja) * | 2008-03-31 | 2009-10-22 | Aica Kogyo Co Ltd | ウレアウレタン樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0125346A1 (en) | 1984-11-21 |
| EP0125346B1 (en) | 1987-11-11 |
| DE3374414D1 (en) | 1987-12-17 |
| US4431753A (en) | 1984-02-14 |
| JPS6366848B2 (enrdf_load_stackoverflow) | 1988-12-22 |
| ATE30731T1 (de) | 1987-11-15 |
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